[CEO Friday] 5 Important Questions to Ask Before Joining a Startup

Based on the sudden spike in applications we’ve seen, there are a lot of people out there with New Year’s resolutions to make the jump. Before you do, I’d recommend asking your employer-to-be the following questions:

How many people do you hire in a typical month? Great people are just hard to come by. I don’t know of any startup that can reliably hire more than one truly fantastic person per month, so if they’re hiring people in droves, they’re not getting the cream of the crop. Hiring is easy if you don’t care who you get: make sure they care.

Who was the last person to quit, and why? People change. Companies change. Even amazing people and amazing companies. A great fit one day might gradually become less great over time, and the best people don’t tolerate that for long. It’s an awkward topic, but see how they handle it. Are they defensive? Introspective? Do they throw their former teammate under the bus, or provide a thoughtful explanation? Is the company better off without that person, or what did they learn and change in response? Nobody likes to be dumped, but if it doesn’t happen sometimes, you aren’t aiming high enough.

When do you intend to raise money, and why? The worst answer is “we just raised so we’re not even thinking about it” — raising is something you should always think about. A better answer is “we have X months of runway before we need to raise again” — this means they’re at least paying attention. But the best answer is “once X happens in the business, then we’ll raise”. It’s subtle, but this question is really determining if a company is burning investor dollars to survive (and without it, they die) or to grow (and without it, they just grow slower). Is the company primarily financed by selling product, or selling itself? To be fair, most startups linger one failed round from certain death, especially in the early days. But be aware that until you are growing under your own steam, you are wholly dependent on investors for your survival — and investors don’t always share your vision.

Can I see where I’ll sit? This actually wraps up a bunch of questions into one. Do they even know? Do they have assigned seating, and if so, can you influence it? Did you meet the people you’ll be sitting next to in the interview process? Is it clean and is there natural light? Is it quiet, or is there music, or just generally noisy? And most important: is it a place you really want to sit 2000+ hours a year? Your workspace is your home away from home, and there is an enormous range between “we just have an awesome office full of diverse regions and you can sit anywhere” and “here’s your awesome standing desk with big monitor”. There are no right answers, but put some real thought into what’s important to you and make sure to factor that in.

And last but not least: What do I want to do accomplish in my life, and how does this help me down that path? This is one you should ask yourself — every day, about everything you do. Our industry is unique in that anybody reasonably good can make money, and with a bit of luck you can make a lot. But all the ways you can spend it get boring much faster than you’d expect. Hard problems and cool technology will keep you occupied for a while, but there are always more problems and more technology, and eventually even those get old. If you’re great — or if you want to be great — your motivations likely run deeper. You have some kind of secret, quiet ambition that is so grand, so audacious, that you are embarrassed to say it out loud. So big that even if you devote the rest of your life to it, you still couldn’t finish it. But so important to you, that you genuinely want to try anyway. Knowing what you want out of life dramatically increases the odds you’ll get it, so figure out what that is, figure out what’s preventing you from doing it right now, and then evaluate whether this startup is going to give you the tools to take the next step. Maybe you lack money, or maybe it’s skill, but more likely you just lack the confidence that comes from being part of a successful team. Make sure your next job is the launchpad for the rest of your life, and not just a landing pad with an extended layover.

I picked five to make the subject link click-baity, but really you should ask a lot of questions. If you’re great, you can probably work anywhere you want. Interview them as much or more than they’re interviewing you. If they’re great too, they’ll recognize you’re worth it and thank you for the effort.

One response to [CEO Friday] 5 Important Questions to Ask Before Joining a Startup

When I first downloaded Expensify ~18-24 months ago, I thought I was getting a receipt-capture app. I then learned it had far more functionality and my company (of consultants) will eventually switch over to this as our standard.

But the blog comments, from you and your team, are real gems and speak volumes to the quality of an organization you are building. And this is coming from a guy who specializes in assessing and building strong organizations.

Great job! Thanks for adding so much more value than I ever expected to receive when I first downloaded “a receipt app.” ☺